Find Family Hotels in Pittsfield, MA
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Aug 24 - Aug 25Tomorrow
Aug 25 - Aug 26This weekend
Aug 28 - Aug 30Next weekend
Sep 4 - Sep 6Our top choices for Pittsfield family-friendly hotels
1. Best Western Plus Berkshire Hills Inn & Suites
Best Western Plus Berkshire Hills Inn & SuitesPittsfield
- Berkshire family fun with free breakfast and ski-area adventures just minutes from winter sports and hiking trails.
NT$3,631
NT$4,056 total
includes taxes & fees
Sep 1 - Sep 2
2. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
- Family adventures await with a heated indoor pool, kid-friendly dining, and spacious suites in the heart of Pittsfield.
NT$3,791
NT$4,235 total
includes taxes & fees
Sep 21 - Sep 22
3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
- Splash into family fun with indoor pool and hot tub—just minutes from Bousquet Ski Area and Tanglewood Music Center.
NT$3,887
NT$4,341 total
includes taxes & fees
Sep 7 - Sep 8
NT$1,978
NT$2,210 total
includes taxes & fees
Aug 25 - Aug 26
5. The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection HotelLee
- Family fun at lakeside retreat with kayaking, fishing, and premium TV channels.
NT$4,062
NT$4,537 total
includes taxes & fees
Sep 14 - Sep 15
NT$5,926
NT$6,619 total
includes taxes & fees
Aug 31 - Sep 1
7. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
NT$3,728
NT$4,786 total
includes taxes & fees
Aug 31 - Sep 1
Top Pittsfield Hotel Reviews
Hotel On North
8/10 Good
"It’s a good place to stay. The rooms are but dark and could you add more lamps to the room?"
Quality Inn Great Barrington
8/10 Good
"Front desk staff was great! Simple hot breakfast was good. Plenty of onsite parking. Conveniently located close to the town and shops."
Best Western Plus Berkshire Hills Inn & Suites
8/10 Good
"It's an old property and it looks it with outdated interior and exterior, stains on really worn carpet, one light out in the room (we lived without it), tiny bathroom and towels so worn out they felt like sandpaper. However, the bed was exactly what I like: mattress was firm enough, bed linens were bright white, pillows were plump enough, and I slept decently. The blinds were truly light-blocking and they closed well. The reason we stayed here was to sleep overnight before heading home the next day, so that objective was achieved. Breakfast included bacon and buffet was stocked. Other breakfast guests were pleasant. Desk staff members did what they were supposed to do. There was a mini fridge, which I wanted so we could have cold drinks for the day we departed. As I recall from reserving two months ago, the rate was a good deal. Would not stay longer than one night, but for a single night, this was a problem-free experience."
The Central Downtown Inn & Suites
10/10 Excellent
"Clean room (suite). Property well maintained. Communication was done via text messages."
Comfort Inn & Suites East Greenbush - Albany
10/10 Excellent
"Nice place"
Berkshire Inn
10/10 Excellent
"Asked for extra towels on a motorcycle in a rain storm and they brought them straitaway and with a smile"
The Yankee Inn
8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Vacation Village in the Berkshires
8/10 Good
"Price - quality =awesome"
The Red Lion Inn
10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
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- Visit Hancock
- Charles H. Baldwin & Sons
- Visit Housatonic
- Norman Rockwell Museum
- Lenox Mountain
- Kushi Institute
- South Lee Vacations
- Mount Greylock State Reservation Visitor Center
- National Shrine of the Divine Mercy
- Visit West Stockbridge
- Pleasant Valley Wilderness Sanctuary
- Visit South Lee
- Greenock Country Club
- Visit Lee
- Bousquet Ski Area
- Canoe Meadows Wildlife Sanctuary
- Visit Lenox
- Frelinghuysen Morris House and Studio
- Visit Middlefield
- Crane Museum of Papermaking
- Animagic Museum of Animation
- Mission House
- Lee Premium Outlets
- Berkshire Botanical Garden
- Visit Lanesborough
- Visit Dalton